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Conformational Equilibrium of 4-Hydroxy- and 4-Acetoxy-4-(3-aryloxy-1-propynyl)-1-(2-ethoxyethyl)piperidinium Salts in Solution

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Abstract

4-Hydroxy- and 4-acetoxy-4-(3-aryloxy-1-propynyl)-1-(2-ethoxyethyl)piperidine hydroclorides in aprotic solvents give rise to equilibrium mixtures of two epimers. In the case of the acetoxy derivatives (in CDCl3) the equilibrium is displaced toward the “less stable” epimer. This may be due to considerable contribution of the skewed boat conformer with intramolecular hydrogen bond.

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Authors and Affiliations

  1. Ministry of Education and Science of Kazakhstan Republic, Bekturov Institute of Chemical Science, ul. Ch. Valikhanova 106, Almaty, 480100, Kazakhstan

    I. A. Poplavskaya, K. B. Bazhykova & K. D. Praliev

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  1. I. A. Poplavskaya
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  2. K. B. Bazhykova
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  3. K. D. Praliev
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Poplavskaya, I.A., Bazhykova, K.B. & Praliev, K.D. Conformational Equilibrium of 4-Hydroxy- and 4-Acetoxy-4-(3-aryloxy-1-propynyl)-1-(2-ethoxyethyl)piperidinium Salts in Solution. Russian Journal of Organic Chemistry 37, 1782–1785 (2001). https://doi.org/10.1023/A:1013999212842

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  • DOI: https://doi.org/10.1023/A:1013999212842

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